


The New Nanny

by faegal04, reigningqueenofwords



Series: Chocolate Cupcakes [1]
Category: Supernatural AU
Genre: Gen
Language: English
Status: Completed
Published: 2019-07-06
Updated: 2019-07-06
Packaged: 2020-06-22 05:45:34
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,168
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19661041
Author URL: https://archiveofourown.org/users/faegal04/pseuds/faegal04, https://archiveofourown.org/users/reigningqueenofwords/pseuds/reigningqueenofwords





	The New Nanny

Being a single father wasn’t what Sam expected life to turn out like. Yet, there he was. Him and his wife, Jess, had divorced after six years of being together, three of those married. He had their twins, Liam and Ava, from Sunday until Wednesday. Jess had them the other days. It was difficult trying to explain to them why mommy and daddy didn’t live together anymore, and why they had two houses now.

Sam was a lawyer. He didn’t deal with upset little kids all day- he dealt with adults. Sadly, he didn’t know which was worse. Jess had moved out Friday, and it was now Sunday. He’d taken off the following week to help the kids adjust, but then he had to go back to work. Hours were hectic at the office, and he would need someone to help out after they got home from preschool, and on school breaks.

The thought made him groan. Interviewing people, putting up with woman after woman making a pass at him, or worse, coming off rude and judgemental. Running a hand through his hair, he grabbed his glass of whiskey and made his way to his home office. Liam and Ava would be back in about an hour, so he figured he’d start the search. Hopefully this wouldn’t be too painful.

After taking a sip from his glass, he set it gently on a coaster to his right. Wetting his lips, he started his search. Of course, he couldn’t call anyone until the next morning when the kids were at school, but it was better to be prepared.

He had lost track of time when he heard the sounds of little feet come running through the house. A grin spread across his face as he got up, walking out to the hall to meet them. Sam crouched, getting knocked over when they gave him a running hug at the same time. “Oh, I missed you guys!” He laughed.

“We missed you, Daddy.” Ava peppered his cheek with kisses.

Liam just hugged him tighter. “Can we go play?” He looked up at Sam’s face, hopeful.

Sam smiled. “Yeah, buddy. Go put your stuff in your room and we’ll go play.”

He didn’t even look at Jess, there wasn’t a point anymore. “Thanks for bringing them back on time, but please Jess in the future-knock first. You don’t live here anymore,” He added that part gently, it was after all her idea to move out. And she was the one that wanted the divorce without trying anything else first.

“Daddy!” Ava yelled from her room. “Can we play pwincess, _please_?” Sam chuckled at his daughter as she fluttered her eyelashes at him, a trick he was sure she learned from one of Dean’s girlfriends.

Jess cleared her throat. “I’ll remember that.” She said simply. “Alright, Ava, give mommy a hug.” She smiled.

Ava turned to Jess and gave her a hug. “Bye, mommy!” She said sweetly.

Liam came running out with his pirate hat and sword. “Arg! Bye, mommy!” He made the face of a pirate.

“Bye, Liam.” She stood up straight. “Bye, Sam.” Her voice was quieter.

Ava turned back to Sam. “Princess time!” She grinned. 

* * *

Sam let the kids stay up longer than usual because he had missed them but when Liam tried to make Ava ‘walk the plank’ off of the coffee table, he knew it was bedtime. He tucked them both in, read them each their favorite story and making sure to turn on night lights, he finally headed back to his office. He was hoping to find at least a couple of prospects for nannies that he could call tomorrow. He poured another shot of whiskey, he grabbed his laptop and got comfortable on the sofa.

After another hour, he called it a night. He had half a page of possibles, with a couple underlined as the ones to call first. Sighing, he cleaned up and made his way to his room. The bed looked much too large for just him, but he had to get used to it.

As he brushed his teeth, he stared at himself in the mirror. He looked like he felt. Although the divorce papers were served to him months ago, having it be final, and Jess move out, made it all the more real. Running his hand through his hair, he decided to focus on the kids, and his career. He couldn’t put himself or the twins through this again.

* * *

The next morning, Sam was awake an hour before his alarm. He used that time to workout and shower. One less thing he would need to squeeze in between getting two four year olds out of bed, fed, dressed, and Ava’s hair done. Then, getting them to school on time.

Sam considered it a successful morning even though the twins were late to school and he was late for work. Ava got a little to rambunctious with her orange juice, dumping it all over her dress then she was crying about it, Sam picked her up without thinking and then he needed to change as well.

Thankfully they made it to school without any other incidents. Sam spent a few minutes talking with their teacher and let her know that he was going to be looking into a nanny. Ms. Ellen mentioned that she knew of a few people if he didn’t have any luck and to be sure to let him know. He nodded feeling much better about finding someone he would trust with his kids at her statement, in case he had a complete washout with the numbers he found.  
Once he was back home, he set himself up on the island in the kitchen. He had a habit of pacing while on the phone. Within ten minutes, he had crossed off three numbers. None of them had available nannies. It was not looking good.

The fourth number was disconnected, and the fifth had a waiting list that was ridiculous. Leaning his hand on the island while he dialed the sixth number, and sighed. As the phone rang, he paced, hand shoved in his pocket. The more numbers he called, the more anxious he got. Yes, he had a week, but he preferred to find someone quickly, and spend the week going over the kids routines. He would prefer to get to know the nanny a bit, so his children weren’t in a stranger’s hands.

“Hello?” The voice sounded to be that of someone in her fifties.

“Hi, I’m in the search for a nanny. I saw your ad in the paper, and was _hoping_ you may have someone available?”

“Well, don’t you sound tall, dark and handsome,” the somewhat raspy voice said.

“E-excuse me?” Sam stammered. “Maybe I have the wrong number?”

“You have the right number, handsome. You’re looking for my granddaughter, Y/N. Now can I get a name to put to this sexy voice, so that I can tell her who’s calling?”

“Umm, My name is Sam Winchester, is she there please, ma’am?”

“She sure is, Sam,” the voice purred his name. “Y/N, sweetheart, there is a gentlemen caller on the phone in need of your _services_. Here, she is handsome, by the way my name is Dorothy but you can call me anything you want-”

“ _Grandma_!!” came a loud a female voice. “Give me that!” He couldn’t help but chuckle. “Hello?”

He had a smile on his face. “Hi, my name is Sam, and I saw your add in the paper. I’m in search of a nanny.” He managed. “I’m sorry, I’ve never needed one before.”

You chuckled. “And I’m sorry about my Grandmother.” You told him. “I’m available at the moment. What is it that you need a nanny for? I mean, how many kids, ages, what times, things like that.” You moved things around, getting out a pen and paper.

“I have four year old twins, a boy and a girl. It would be a part-time position Monday thru Wednesday in the afternoon with some evenings if court runs over or I need to meet with a client later than normal business hours. Those don’t happen all that often,” Sam hurried to add. “The kids are in preschool, so they would need picked up, if that is something you do?”

“I can do that. I will need to make sure that the boosters seats I have are at their level, and not expired. I try to keep them as up to date as possible.” You told him kindly. “And, if it’s possible, I _prefer_ to spend a day or two with the whole family? This way I know them, they know me, and we can discuss any concerns that may come up. Is that a problem?”

“No, actually that is perfect. I took the week off from work to find someone, and was hoping that we could spend some time together. It would be me and the kids, I’m recently divorced,” Sam finished quietly.

“I’m sorry to hear that,” you said gently. “Well, seeing that today is Monday, if you are available today maybe we could meet at the park this afternoon?”

He let out a small sigh of relief. “I get the kids from school about three. What time would be good for you?”

“I’m free all day, actually.” You chuckled. “I’m just helping my Grandmother out around her store. I’d be more than happy to get out for a bit.”

“Okay.” He laughed. “We can meet at the swingsets about three-fifteen, if that works for you.”

“Perfect! I’m looking forward to meeting you and the kids then. If you give me your email address, I can email my resume, references and my picture,” you said. You took Sam’s email address down, ending the call you kissed your grandmother goodbye letting her know that you had to go home so you could email everything to tall, dark and handsome and change.

* * *

Sam pushed the rest of the numbers off to the side for now. He wouldn’t throw them away until he was sure that you were a good fit for the family. You sounded nice, so he was crossing his fingers. Now he just had the rest of the school day to check work e-mails, answer any voice mails he may have, and figure out what kinds of questions that he needed to ask. 

* * *

You didn’t live too far from your grandmother’s shop, so you made sure to get the e-mail out first. Then you’d shower and get ready. You threw on a pair of faded jeans, a [peasant blouse](https://t.umblr.com/redirect?z=http%3A%2F%2Fwww.fashiongonerogue.com%2Fpeasant-blouse-shop%2F&t=YTVkZGI2YzM5OWU4NGRhZThkNDc4NWNlYTAzOGU1MDNjODZiMWFlYyx1c05RR29Feg%3D%3D&b=t%3ABztGC4epmrhiuq6hmkrbTA&p=https%3A%2F%2Freigningqueenofwords.tumblr.com%2Fpost%2F164082415456%2Fthe-new-nanny&m=1), and a pair of tennis shoes to complete your outfit, kept the makeup light and pulled your hair up into a messy bun.

You made it to the park right at three, so you found a bench close to the swings to wait for Sam. You watched some of the kids playing, laughing when you saw how happy they were swinging and going down the slide. You saw a very handsome, tall man wearing a plaid shirt and jeans walking towards you, a little girl on one side and a little boy on the other. The little boy was the spitting image of the man holding his hand, you saw him laugh at something his sister said and both kids laughed showing off dimples. Looking up to their dad, you saw that he smiled down at whatever was said and he also had dimples that made your heart stutter. Boy, Grandma was going to be happy that she called it. This man was tall, dark and handsome.

Standing up when he was closer, you smiled at him. “Sam?” You greeted. 

He looked up at you. “That would be me.” He chuckled. “This is Ava, and this is Liam.” He introduced them.

“Hi!” They said at the same time.

You crouched to be eye level with him. “Now, there’s a bakery right across the street. If it’s okay with your _dad_ , after I’ll get you each a cupcake or a cookie. How’s that sound?” You smiled at them, quickly earning a smile back.

“ _Chocolate_ cupcakes?” Ava said with a smile. Liam nodded in agreement.

Sam chuckled, “They definitely have a sweet tooth, afraid they got that from me.”

You winked at both of them and said, “Guess what, I like chocolate cupcakes too, they’re my _favorite_.”

Ava tugged on Sam’s hand, to pull him down closer to her, she still had to stand on her tiptoes to whisper in his ear. “Daddy, she’s pretty like a princess. I like her.” Sam grinned knowing that you had heard her whisper, being four and all she was still getting the whole whisper thing down. You blushed when Sam nodded his head in agreement with Ava’s statement.

Standing, you looped your thumbs in your pockets. “So, what would you like to know? Seeing as you’re looking for someone to care for you kids, I’m sure that you’d like to know whatever you can.” You chuckled.

“Uh…” He chuckled himself, having never done this before. “How long have you been a nanny?”

“Well, I started babysitting when I was 14, did that all the way through college, and then took some courses, and been doing it since.” You shrugged. “I like kids.”

Ava grinned at you. “Do you have any?”

You shook your head, chuckling. “No. No kids. I have a fish, but that’s it. His name’s Casper.” You’d have loved a dog, or a cat, but there was no telling if a kid you watched would be allergic. “What’s your favorite part of the park? Might as well play while we’re here, right?”

“I like the swings best,” Ava said with a smile.

You nodded at her, “I like the swings, too, they make me feel like I’m flying like a fairy.” Ava nodded excitedly at your comment.

Liam looked up at his dad and rolled his eyes, “Girls,” he said with a groan.

Sam chuckled at his son, “You’ll feel different one day, buddy, _trust_ me.”

“What’s your favorite? My second favorite would have to be the merry go round.” You smiled at him.

“I like the monkey bars, I need help right now with ‘em cause I’m little. But daddy says one day I will get as big as him and I will be able to do it all by myself,” Liam said with a proud smile.

“Pfft, if you get as big as your dad you will be able to get across the monkey bars _walking_ , little man.”

“Uncle Dean!” Both kids yelled and took off for the bow legged man coming their way.

You chuckled. “Favorite uncle, I take it?”

“Only uncle.” He shrugged. “Do you have any siblings?”

“One older brother- Cas.”

Dean hobbled over to Sam’s side with Ava standing on one of his feet and her arms wrapped around his leg. He had Liam over his shoulder. Ava started giggling. ”You walk like Franksteen, Uncle Dean.” Ava grinned up at you. “This is Uncle Dean!”

“Hi, Uncle Dean.” You laughed. 

Dean smirked at you and cocked an eyebrow. “Well hello sweetheart. You don’t have to call me Uncle, but you _can_ call me da-”

“Dean, I swear to God if you finish that sentence I will kill you,” Sam said his face reddening. “This is Y/N, she might be the kids new nanny.”

Swinging Liam down into his arms, Dean laughed looked at his nephew and said, “Dude, she’s hot. Think she could be my nanny, too?”

You looked at Sam. “We could always introduce him to Dorothy. They seem to have _about_ the same mind set.” There was a smirk on your face as you turned to Dean. “I know someone who would _love_ to just eat you up…”

Sam laughed hard when you mentioned your grandmother. “I agree, she’s _exactly_ his type.”

“She used to be a showgirl in Vegas, she still brags that she can kick above her head and that she is quote, _quite bendy_ ,” you snickered.

Dean licked his lips automatically. “She look anything like you?”

You nodded. “I’ve been told we have the same eyes, but Sam can give you her number. I’m going to take Ava here to the swings. How’s that, kiddo?” You smiled at her and offered her your hand.

* * *

The rest of the afternoon at the park went well. You took both kids to the bakery and got them and Sam a chocolate cupcake, when you got back with the kids and handed him his cupcake, he blushed which was the most adorable thing you had ever seen.

Sam asked if you would be willing to come over to the house tomorrow evening. That way you could see how dinner would go and bathtimes just in case. You both felt fairly confident that this was going to work out for the good. By the time Wednesday rolled around, you were going to pick up the kids at the preschool and bring them home so that Sam could introduce you to Jess, since you would be the one with the kids when she came to pick them up.

You pulled up to the preschool and parked. Sam had said he’d added you to the list of people allowed to pick up the kids, so you made your way into the the building. You’d put the boosters in the back of your car, and had stopped at the bakery, buying some mini-cupcakes for dessert that night. Half chocolate, half strawberry. You hoped that was okay.

You made sure to stop and show your ID, since you were a new addition to the list. Which, you didn’t mind. This was something that you were used to.

The kids smiled when they saw you and waved. You smiled and waved back. “Ready to get home?” You asked.

“Yup!” Liam agreed.

You took the kids hands and led them to your car, each trying to tell you about their day. “Okay, okay.” You laughed. “How about Ava tell me one thing, then Liam. We’ll go back and forth all the way back to your house. Does that sound fair?”

* * *

By the time you got them out of the car, you were pretty sure you knew their teacher’s names, their favorite animals, their favorite colors, best friend’s names, kids they didn’t like, their favorite food, and what they wanted to be when they grew up. Boy, could those kids talk!

You got them in the house, both of them taking off to find Sam. He was playing Marco Polo with them and you chuckled every time you hear Liam groan when he thought he had found him. You sat the cupcakes on the island and moved to take the chicken out of the fridge, when you heard a gasp from behind you.

“Who are you? And why are you in my house?”

You turned around slowly, “Uh my name is Y/N Y/L/N. I’m a nanny.”

“ ** _SAM_**!” Jess yelled.


End file.
